Oxymercuration Video Lessons

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Problem: Predict the product(s).

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FREE Expert Solution

We’re being asked to determine the products of the given reaction.

Recall that alkenes are converted to alcohols via oxymercuration-reduction:

This occurs in three steps:

(1) electrophilic addition – the alkene attacks Hg(OAc)2, forming the cyclic mercurinium ion. Since a cyclic intermediate is formed, rearrangement is not possible for this reaction.

(2) nucleophilic attack – water attacks the cyclic mercurinium ion. This follows Markovnikov’s rule, where water attacks the more-substituted carbon. The stereochemistry of this reaction is anti, where –OH and –HgOAc will be trans to each other.

(3) reduction – NaOH and NaBH4 react with the intermediate to form the alcohol.

81% (273 ratings)
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Predict the product(s).

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